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AS
CHEMISTRY
Paper 2 Organic and Physical Chemistry

Thursday 23 May 2019 Morning Time allowed: 1 hour 30 minutes

Materials
For Examiner’s Use
For this paper you must have:
• the Periodic Table/Data Sheet, provided as an insert (enclosed) Question Mark
• a ruler with millimetre measurements
1
• a scientific calculator, which you are expected to use where appropriate.
2
Instructions 3
• Use black ink or black ball-point pen. 4
• Fill in the boxes at the top of this page.
5
• Answer all questions.
• You must answer the questions in the spaces provided. Do not write outside 6
the box around each page or on blank pages. 7
• All working must be shown. 8
• Do all rough work in this book. Cross through any work you do not
want to be marked. 9
Section B
Information TOTAL
• The marks for questions are shown in brackets.
• The maximum mark for this paper is 80.

Advice
You are advised to spend about 65 minutes on Section A and 25 minutes on Section B.

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Section A box

Answer all questions in this section.

0 1 The structures of three organic compounds A, B and C are shown.

These compounds can be distinguished by simple test-tube reactions.

For each pair of compounds in questions 01.1 and 01.2, give a reagent
(or combination of reagents) that could be added separately to each compound to
distinguish between them.

State what is observed in each case.

0 1 . 1 Compounds A and B
[3 marks]

Reagent

Observation with A

Observation with B

0 1 . 2 Compounds A and C
[3 marks]

Reagent

Observation with A

Observation with C
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0 2 Bromoethane reacts with potassium cyanide to form compound D. box

CH3CH2Br + KCN → CH3CH2CN + KBr

Compound D

0 2 . 1 Outline the mechanism for this reaction.

[2 marks]

0 2 . 2 Give the IUPAC name of D.

[1 mark]

0 2 . 3 Calculate the percentage atom economy for the formation of D in this reaction.

Give your answer to the appropriate number of significant figures.

[2 marks]

% atom economy 5

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0 3 This question is about enthalpy changes. box

0 3 . 1 A student determined the enthalpy of combustion of cyclohexane (C6H12).

The student
• placed a pure sample of cyclohexane in a spirit burner
• placed the spirit burner under a beaker containing 50.0 g of water and ignited
the cyclohexane
• extinguished the flame after a few minutes.

The results for the experiment are shown in Table 1.

Table 1

Initial temperature of the water / °C 19.1

Initial mass of spirit burner and cyclohexane / g 192.730

Final mass of spirit burner and cyclohexane / g 192.100

The student determined from this experiment that the enthalpy of combustion of
cyclohexane is –1216 kJ mol−1

Use the data to calculate the final temperature of the water in this experiment.

The specific heat capacity of water = 4.18 J K–1 g–1

The relative molecular mass (Mr) of cyclohexane = 84.0
[4 marks]

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Final temperature of the water °C

0 3 . 2 A data book value for the enthalpy of combustion of cyclohexane is –3920 kJ mol−1

The student concluded that the temperature rise recorded in the experiment
was smaller than it should have been.

Suggest a practical reason for this.

[1 mark]

Question 3 continues on the next page

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0 3 . 3 Table 2 gives some values of standard enthalpies of combustion (∆cHo). box

Table 2

Substance C(s) H2(g) C6H12(l)

Standard enthalpy of
–394 –286 –3920
combustion, ∆cHo / kJ mol–1

Use the data in Table 2 to calculate the enthalpy change for the reaction
represented by this equation

6 C(s) + 6 H2(g) → C6H12(l)

[3 marks]

Enthalpy change kJ mol–1 8

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0 4 This question is about fossil fuels. box

0 4 . 1 The petrol fraction from crude oil contains octane (C8H18).

Give an equation for the complete combustion of octane.

[1 mark]

0 4 . 2 The combustion of petrol in car engines produces the pollutant

nitrogen monoxide.

Give an equation for a reaction that removes nitrogen monoxide in

a catalytic converter.
[1 mark]

Question 4 continues on the next page

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0 4 . 3 Sulfur dioxide is produced in the combustion of fossil fuels. The total emissions box

of sulfur dioxide in the UK have fallen dramatically since 1970.

Sulfur dioxide is now removed from the flue gases in power stations by reaction
with calcium oxide.

CaO + SO2 → CaSO3

In 1970, the total UK emissions of sulfur dioxide were 6.49 million tonnes
(1 tonne = 1000 kg).

Calculate the mass, in kilograms, of calcium oxide needed to react with this
mass of sulfur dioxide.

Give your answer in standard form.

[2 marks]

Mass of calcium oxide kg 4

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0 5 Methanol (CH3OH) is an important alcohol with many uses. box

0 5 . 1 Draw a diagram to show how two methanol molecules interact with each other
through hydrogen bonding in the liquid phase.

Include all partial charges and all lone pairs of electrons in your diagram.
[3 marks]

0 5 . 2 The bond angle around the oxygen atom in methanol is slightly smaller than the
regular tetrahedral angle of 109.5°

Explain why this bond angle is smaller than 109.5°

[1 mark]

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0 5 . 3 Methanol is made by the reaction of carbon monoxide with hydrogen. box

CO + 2 H2 ⇌ CH3OH ∆H = –91 kJ mol–1

The reaction uses a copper-based catalyst, a pressure of 10 MPa and a

temperature of 550 K

These conditions are used to provide a balance between equilibrium yield,

reaction rate and cost.

Describe how the use of a catalyst, and changes in pressure and temperature,
each affect equilibrium yield, reaction rate and cost.
[6 marks]

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10

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0 6 Propene reacts with concentrated sulfuric acid to form two isomers, E and F. box

The structure of E is shown.

0 6 . 1 Name and outline the mechanism for the formation of E in this reaction.
[5 marks]

Name of mechanism

Mechanism

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0 6 . 2 Draw the structure of F. box

[1 mark]

0 6 . 3 Explain why more of isomer E than isomer F is formed in this reaction.

[2 marks]

Turn over for the next question

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0 7 Propanedioic acid contains two carboxylic acid groups. It is a solid organic acid that is box

soluble in water.

0 7 . 1 Draw the skeletal formula of propanedioic acid.

[1 mark]

0 7 . 2 Describe how to prepare 250 cm3 of an aqueous standard solution of

propanedioic acid containing an accurately measured mass of the acid.
Include essential practical details in your answer.
[6 marks]

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0 7 . 3 Calculate the mass, in mg, of propanedioic acid (Mr = 104.0) needed to prepare
250 cm3 of a 0.00500 mol dm–3 solution.
[2 marks]

Mass of propanedioic acid mg 9

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0 8 Propanal can be prepared by the oxidation of propan-1-ol with box

acidified potassium dichromate(VI).

An ionic equation for this reaction is

3 CH3CH2CH2OH + Cr2O72– + 8 H+ → 3 CH3CH2CHO + 2 Cr3+ + 7 H2O

0 8 . 1 Calculate the minimum volume, in cm3, of

0.40 mol dm–3 potassium dichromate(VI) solution needed to oxidise
6.0 cm3 of propan-1-ol to propanal.

Mr of propan-1-ol = 60.0
Density of propan-1-ol = 0.80 g cm–3
[3 marks]

Minimum volume cm3

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0 8 . 2 The reaction is done in a pear-shaped flask. box

Complete the diagram to show the assembled apparatus needed to prepare

propanal from propan-1-ol in this way.

Label the diagram.

[3 marks]

Turn over for the next question

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There are no questions printed on this page box

DO NOT WRITE ON THIS PAGE

ANSWER IN THE SPACES PROVIDED

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0 9 The compound 1,2-dichlorotetrafluoroethane is a CFC that was previously used in box

refrigerators as a coolant.

0 9 . 1 Molecules of 1,2-dichlorotetrafluoroethane can break down in the upper atmosphere

to form chlorine radicals.

Give an equation to show the breakdown of one molecule of

1,2-dichlorotetrafluoroethane to form one chlorine radical and one other species.
[1 mark]

0 9 . 2 Give two equations to show how chlorine radicals catalyse the decomposition of
ozone.
[2 marks]

Question 9 continues on the next page

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0 9 . 3 Butane can be used as a replacement for CFCs in refrigerators. box

During its use, the butane is repeatedly converted from liquid to gas and then
back to liquid. Liquid butane expands as it turns into a gas.

• Calculate the volume, in cm3, of 38.8 g of butane gas at 272 K and 101 kPa
(the gas constant R = 8.31 J K–1 mol–1)
(Mr of butane = 58.0)

• Calculate the volume, in cm3, of 38.8 g of liquid butane.

(density of liquid butane = 0.60 g cm–3)

• Use your answers to calculate the factor by which butane expands in volume
when it changes from a liquid to a gas.

Show your working.

[6 marks]

Volume of butane gas cm3

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Volume of liquid butane cm3

Expansion factor 9

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Section B box

Answer all questions in this section.

Only one answer per question is allowed.

For each answer completely fill in the circle alongside the appropriate answer.

CORRECT METHOD WRONG METHODS

If you want to change your answer you must cross out your original answer as shown.

If you wish to return to an answer previously crossed out, ring the answer you now wish to select
as shown.

You may do your working in the blank space around each question but this will not be marked.
Do not use additional sheets for this working.

1 0 A ‘drink-driving’ offence is committed if the blood alcohol level of a driver is over

80 mg of ethanol per 100 cm3 of blood.
What is the concentration, in mol dm–3, of ethanol if there are 80 mg of ethanol
(Mr = 46.0) per 100 cm3 of blood?
[1 mark]

A 0.00017

B 0.0017

C 0.017

D 1.7

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1 1 Which statement is correct for the distribution curve of molecular energies in a gas? box

[1 mark]

A The curve is symmetrical about the maximum.

B There are always some molecules with zero energy.

The position of the maximum of the curve is not dependent on the

C
temperature.

The mean energy of the molecules is greater than the most

D
probable energy of the molecules.

1 2 When one mole of ammonia is heated to a given temperature, 50 % of it dissociates

and the following equilibrium is established.

1 3
NH3(g) ⇌ N (g) + H2(g)
2 2 2

What is the total amount, in moles, of gas in this equilibrium mixture?

[1 mark]

A 1.5

B 2.0

C 2.5

D 3.0

1 3 Which compound is not an isomer of the following compound?

[1 mark]

A CH3CH2COCH3

B CH3CH═CHCH2OH

C (CH3)2CHCHO

D CH2═CHCH2CHO

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1 4 How many isomers are there of C3H9N? box

[1 mark]

A 2

B 3

C 4

D 5

1 5 Which equation represents a propagation step?

[1 mark]

A •CH2Cl + Cl•  CH2Cl2

B •CH3 + •CH3  C2H6

C Cl2  Cl• + Cl•

D CH3Cl + Cl•  •CH2Cl + HCl

1 6 Which compound can react with ammonia to produce propylamine?

[1 mark]

A CH3CH═CH2

B CH3CH2CH2OH

C CH3CH2CH2Br

D CH3CH2CH3

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1 7 Which statement is not correct about CH2═C(CH3)CH2Br? box

[1 mark]

A It displays E-Z isomerism.

B It forms an addition polymer.

C It reacts with electrophiles.

D It decolourises bromine water.

1 8 Which compound can be oxidised to form (CH3)2CHCOCH3?

[1 mark]

A 2-methylpropan-1-ol

B 2,2-dimethylpropanol

C 2-methylbutan-2-ol

D 3-methylbutan-2-ol

1 9 Which species can act as a nucleophile?

[1 mark]

A NH4+

B CH3OH

C CH4

D H+

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2 0 Which alcohol forms a mixture of alkenes when dehydrated? box

[1 mark]

A propan-1-ol

B propan-2-ol

C pentan-1-ol

D pentan-2-ol

2 1 Which compound has the highest boiling point?

[1 mark]

A CH3CH2CH2Br

B CH3CH2CH2F

C CH3CH2CHO

D CH3CH2COOH

2 2 Which compound could not be produced by reacting 2-bromo-3-methylbutane with

sodium hydroxide?
[1 mark]

A 2-methylbut-1-ene

B 3-methylbut-1-ene

C 2-methylbut-2-ene

D 3-methylbutan-2-ol

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2 3 The infrared spectrum of an organic compound is shown. box

Which compound produces this spectrum?

[1 mark]

A ethanoic acid

B 4-hydroxybutanone

C propan-1-ol

D prop-2-en-1-ol

Turn over for the next question

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2 4 The heat released when 1.00 g of ethanol (Mr = 46.0) undergoes complete box

combustion is 29.8 kJ

What is the heat released by each molecule, in joules, when ethanol undergoes
complete combustion?

(the Avogadro constant L = 6.022 × 10 23 mol–1)

[1 mark]

A 2.28 × 10–18 J

B 4.95 × 10–20 J

C 2.28 × 10–21 J

D 4.95 × 10–23 J
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END OF QUESTIONS

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